title: Triazole biotin: a tight-binding biotinidase-resistant conjugate.
abstract: The natural amide bond found in all biotinylated proteins has been replaced with a triazole through CuAAC reaction of an alkynyl biotin derivative. The resultant triazole-linked adducts are shown to be highly resistant to the ubiquitous hydrolytic enzyme biotinidase and to bind avidin with dissociation constants in the low pM range. Application of this strategy to the production of a series of biotinidase-resistant biotin-Gd-DOTA contrast agents is demonstrated.
authors.affiliation: EaStCHEM School of Chemistry, University of Edinburgh, West Mains Road, Edinburgh, EH9 3JJ, UK. Alison.Hulme@ed.ac.uk.
authors.forename: Anne I
authors.initials: AI
authors.lastname: Germeroth
authors.forename: Jill R
authors.initials: JR
authors.lastname: Hanna
authors.forename: Rehana
authors.initials: R
authors.lastname: Karim
authors.forename: Franziska
authors.initials: F
authors.lastname: Kundel
authors.forename: Jonathan
authors.initials: J
authors.lastname: Lowther
authors.forename: Peter G N
authors.initials: PG
authors.lastname: Neate
authors.forename: Elizabeth A
authors.initials: EA
authors.lastname: Blackburn
authors.forename: Martin A
authors.initials: MA
authors.lastname: Wear
authors.forename: Dominic J
authors.initials: DJ
authors.lastname: Campopiano
authors.forename: Alison N
authors.initials: AN
authors.lastname: Hulme
mesh_terms: D001710:Biotin / Q000737:chemistry*; D043523:Biotinidase / Q000737:chemistry*; D045744:Cell Line, Tumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D014230:Triazoles / Q000737:chemistry*
chemical_list: D014230:Triazoles; D001710:Biotin; D043523:Biotinidase